tert-Butyl 2-(S)-trifluoromethanesulfonyl phenyllactate | 170555-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: tert-Butyl 2-(S)-trifluoromethanesulfonyl phenyllactate
• 英文别名: (-)-(2S)-trifluoromethanesulfonyloxy-3-phenyl-propionic acid tert-butyl ester；tert-butyl (2S)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate
• CAS: 170555-66-5
• 化学式: C₁₄H₁₇F₃O₅S
• 分子量: 354.347
• InChiKey: OXZLDLQVWIGMKK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-Butyl 2-(S)-trifluoromethanesulfonyl phenyllactate 在 (S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以30%的产率得到tert-butyl cinnamate
  参考文献：
  名称：

  Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of .alpha.-Trifluoromethanesulfonate Substituted Esters

  摘要：

  The addition of chiral imides to alpha-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields. Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products. The reactions proceed through the predicted S(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.

  DOI：

  10.1021/jo00120a022
• 作为产物：
  描述：

  L-(-)-3-苯基乳酸 在 吡啶 、 copper(l) chloride 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 tert-Butyl 2-(S)-trifluoromethanesulfonyl phenyllactate
  参考文献：
  名称：

  Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of .alpha.-Trifluoromethanesulfonate Substituted Esters

  摘要：

  The addition of chiral imides to alpha-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields. Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products. The reactions proceed through the predicted S(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.

  DOI：

  10.1021/jo00120a022

文献信息

• Zinc‐Catalyzed Enantiospecific sp³–sp³ Cross‐Coupling of α‐Hydroxy Ester Triflates with Grignard Reagents
  作者：Christopher Studte、Bernhard Breit

  DOI：10.1002/anie.200800733

  日期：2008.7.7
• Asymmetric Synthesis of 2,3-Disubstituted Succinates via Chiral Oxazolidinone Controlled Displacement of .alpha.-Trifluoromethanesulfonate Substituted Esters
  作者：Carl P. Decicco、David J. Nelson、Ronald L. Corbett、Jason C. Dreabit

  DOI：10.1021/jo00120a022

  日期：1995.7

  The addition of chiral imides to alpha-trifluoromethanesulfonate esters gave chiral 2,3-disubstituted succinates with moderate to excellent diastereoselectivity and in good overall chemical yields. Both syn and anti chiral products are attainable via this methodology, with generally better diastereoselectivity and chemical yields observed in the production of the syn products. The reactions proceed through the predicted S(N)2 displacement of the triflate leaving group, as inferred from the absolute configuration of the products.